Metathesis is a catalytic reaction generally known in the art that involves the interchange of alkylidene units among compounds containing one or more double bonds (e.g., olefinic compounds) via the formation and cleavage of the carbon-carbon double bonds. Metathesis may occur between two like molecules (often referred to as self-metathesis) and/or it may occur between two different molecules (often referred to as cross-metathesis). Self-metathesis may be represented schematically as shown in Equation I.R1—CH═CH—R2+R1—CH═CH—R2R1—CH═CH—R1+R2—CH═CH—R2  (I)
wherein R1 and R2 are organic groups.
Cross-metathesis may be represented schematically as shown in Equation II.R1—CH═CH—R2+R3—CH═CH—R4R1—CH═CH—R3+R1—CH═CH—R4+R2—CH═CH—R3+R2—CH═CH—R4+R1—CH═CH—R1+R2—CH═CH—R2+R3—CH═CH—R3+R4—CH═CH—R4  (II)
wherein R1, R2, R3, and R4 are organic groups.
In recent years, there has been an increased demand for environmentally friendly techniques for manufacturing materials to take the place of materials typically derived from petroleum sources. For example, researchers have been studying the feasibility of manufacturing biofuels, waxes, plastics, and the like, using natural oil feedstocks, such as vegetable and seed-based oils. In one non-limiting example, metathesis catalysts are used to manufacture candle wax, as described in PCT/US2006/000822, which is herein incorporated by reference. Metathesis reactions involving natural oil feedstocks offer promising solutions for today and for the future.
The metathesized natural oil-based compositions may have low melting points that are suitable for use in certain applications, such as candle waxes. However, it would be advantageous to develop higher melting point waxes that utilize the metathesized natural oil as well. Such waxes would have the potential to replace microcrystalline polyethylene or Fisher-Tropsch based waxes. Additionally, higher melting point waxes could used as a structuring agent in cosmetics, emulsifying/thickening agent, slip agent, internal lubricant, pigment dispersant, or a hot melt adhesive, as well as other wax applications.